Reacción #2195497

ord-785bf6da1b014f6d91aa47772a600156

Ecuación de reacción

CCOC(=O)CC(=O)CC(=O)OCC
diethyl 3-oxopentanedioate
O=C([O-])O.[Na+]
sodium bicarbonate
COc1ccc(P2(=S)SP(=S)(c3ccc(OC)cc3)S2)cc1
Lawesson's reagent
→
CCOC(=O)CC(=S)CC(=O)OCC
title compound
CCOC(=O)CC(=S)CC(=O)OCC
Diethyl 3-thioxopentanedioate

Reactantes

CCOC(=O)CC(=O)CC(=O)OCC
diethyl 3-oxopentanedioate
O=C([O-])O.[Na+]
sodium bicarbonate
COc1ccc(P2(=S)SP(=S)(c3ccc(OC)cc3)S2)cc1
Lawesson's reagent

Reactivos

Ninguno

Disolventes

Cc1ccccc1
toluene

Condiciones de reacción

Condiciones detalladas
See reaction.notes.procedure_details.

Tratamiento posterior

  1. 1
    Temperaturathen heat
  2. 2
    Temperaturaunder reflux for 5 h
  3. 3
    TemperaturaCool
  4. 4
    Filtraciónfilter
  5. 5
    Concentraciónconcentrate in vacuo
  6. 6
    OtroPurify the residue by silica gel chromatography

Procedimiento

Dissolve 14.1 mmol of diethyl 3-oxopentanedioate in 15 mL of toluene under argon add 49.4 mmol of sodium bicarbonate and 15.1 mmol of Lawesson's reagent. Stir for 1 h at room temperature then heat under reflux for 5 h. Cool, filter, and concentrate in vacuo. Purify the residue by silica gel chromatography using ethyl acetate/hexanes eluant to yield the title compound.

Fuente

DOI: 10.6084/m9.figshare.5104873.v1Patente: US07514068B2uspto-grants-2009_04